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118 Fun Dating Icebreaker Questions

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Dating icebreaker questions are a great way of getting to know your date and ensuring that you have something to talk about.

These fun dating icebreaker questions will ensure you don’t run out of talking points and that your date with the guy or girl you like goes smoothly. One of the biggest concerns on a date is not knowing what to talk about, especially if you’re on a date with your crush.

With this list of things to talk about on a date, you can choose which questions you want to ask and which ones you feel your date will be most receptive to.

Whichever of these questions you choose to ask, we’re sure you’ll have plenty of interesting conversations as a result!

Best Dating Icebreaker Questions

1. Describe the proudest moment in your life?  

dating icebreaker questions proudest moment of your life

2. What story from your younger years always makes you cringe?

3. Have you ever been in a situation where it was just too good to be true? 

4. What book/TV series or film had the most significant impact on how you live your life?

5. Have you ever met anyone famous? What was the situation, and were you starstruck? 

6. Where in the world have you always wanted to travel to? 

7. If you found a bag with $2 million in it, would you report it to the authorities or keep it for yourself?

8. What’s the most embarrassing dating story you have?

9. What’s the best prank you’ve ever played on a friend or family member?

10. What’s the most embarrassing thing to happen to you this year? 

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11. If you were a pro boxer/wrestler, what would your entrance music be?

12. Do you think you’re someone that enjoys city life, or do you enjoy being in the country more? 

13. If you could have an endless supply of any food, what would it be and why?

14. What advice would you give your teenage self if you could go back in time? 

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15. Do you have a close relationship with your parents and siblings? 

16. What are your 10 favorite cities in the world? 

17. If you could bring any trend back from the dead, what would it be and why?

18. What’s the best live music event you’ve been to? 

19. Tell me about the worst date you’ve been on? Why was it so bad?  

20. What three people would you want with you if the world was going through a zombie apocalypse? Why these three people?

21. What’s the most embarrassing thing you’ve done while being drunk?

22. If you had no financial worries, how would you spend the rest of your life?

23. What’s the best pickup line you use all the time?

24. Describe what, in your opinion, makes a great first date? 

25. What accomplishment are you most amazed you achieved?

26. If you could travel back to any time, what period would you travel to and why?

27. What first impression do you want to give people when you meet them for the first time?

28. If you were stranded on a desert island, what’s one thing you would bring with you? 

dating icebreaker questions what would you bring on a desert island

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29. When was the last time you wore fancy dress? What character did you go as?

30. If you had to relocate for work, which country would you love to move to and why? 

31. Do you like any extreme sports? 

32. What were you like as a kid? Were you well-behaved, naughty, shy etc.? 

33. Did you excel in anything in school 

34. Do you have a specific morning routine? If so, what is it? 

35. Do you believe in life after death? Have you ever experienced anything paranormal? 

36. Do you like tea and coffee?  

37. What’s your go-to drink on a night out? 

38. What do you think you could improve about your personality? 

39. What relationship pet peeves do you have?

40. Have you ever collected anything in the past?

41. Did you have a celebrity crush growing up? Are they still your crush now? 

42. What’s the most adventurous things you’ve ever done? 

dating icebreaker questions what's the most adventurous thing you've done

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43. What’s the most spontaneous thing you’ve ever done? 

44. What’s the most incredible skill?  

45. Do you have any hidden talents? 

46. What’s been your best vacation and why?

47. What’s the number one thing you would change about your body if you could? 

48. What’s the best life advice you’ve received from someone? 

49. What life advice would you give to your children? 

50. What do you think the best parts of your personality are? 

51. What’s the best job you’ve ever had? Why was it so good? Do you wish you could go back to it? 

52. What’s the worst job you’ve had? Why was it so bad? How long were you there for? 

53. What’s always been a dream career for you? Why haven’t you pursued it? 

Fun Dating Icebreaker Questions To Ask

54. What was your most embarrassing moment when you were a teenager? 

55. Are you currently trying to improve any aspect of yourself?

56. What’s the most disgusting thing you’ve ever eaten? 

dating icebreaker questions disgusting food

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57. What’s the worst thing you did as a kid, and you managed to get away with it? 

58. What’s the silliest memory you have with all your friends? 

59. What was the first music album you ever listened to? 

60. What were you scared of as a child? Clowns, the dark etc.? 

61. What’s the funniest thing to happen to you this week?

62. If you were going to get a tattoo, what would it be of, and what meaning would it have to you?  

63. What’s the worst tattoo someone could pick for you? 

64. If you had to create a quote about your life, what would it be? 

65. What’s your favorite piece of clothing, no matter how old or embarrassing, you still love to wear today? 

66. How do you feel about the 5-second rule when dropping food on the floor? 

67. Do you enjoy exercising? What’s your favorite way to work out?

68. If you could eliminate one type of food, what food would it be and why? 

69. What invention do you think will be huge in the years to come? 

70. If you were super famous, what brand would you endorse? 

dating icebreaker questions if famous what brand would you endorse

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71. You may already have it, but what does your dream home look like?

72. If you had to describe yourself as an alcoholic drink, what drink would you be and why? 

73. What’s the most embarrassing haircut you’ve ever had? Have you got any pictures? 

74. What advert commercial soundtrack always gets stuck in your head every time you listen to it? 

75. If you had the opportunity to change a law, what law would you change and why? 

76. What well-known person would you never want to meet? 

77. What dance moves are you well known for with your friends? 

Get To Know You Dating Icebreaker Questions To Ask

78. What family traditions do you have? Will you continue them when you have a family of your own? 

79. What’s something people would be surprised to know about you? 

80. Would you rather work or be someone that lives a life of leisure? 

81. What character did you used to dress up as a lot as a child? 

82. What band or musician are you embarrassed that you like? 

83. What random skill would you be interested to learn? 

84. When in your life have you felt most alive? 

dating icebreaker questions when have you felt most alive

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85. What’s the most extraordinary gift a partner has ever given you? 

86. Do you enjoy cooking for yourself, or would you prefer to order food from a restaurant?

87. Have you ever done something wrong and blamed others around you? 

88. If you could choose to stay at any age forever, what age would you choose and why? 

89. If you had the choice of finding true love or winning $50 million, what would you choose? 

90. What artist or band, whether they’re alive or not, would you want to play at your wedding? 

91. What’s your favorite guilty pleasure?

92. When dating someone, what do you think is your most-used emoji?

93. If you had no choice but to marry one of your friends’ partners, who would it be and why? 

94. What’s the most unusual activity you’ve done on a date?

95. What’s one thing you always lose? 

Deep Dating Icebreaker Questions To Ask

96. What challenges do you currently face in day-to-day life? 

97. When dating, what compliment do people give you the most?

98. What’s the best praise you’ve ever received from someone? 

dating icebreaker questions best praise you've received

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99. What’s one thing you miss from childhood?  

100. What can you easily say is the best thing you’ve done in your life? 

101. If you could be guaranteed one thing in life, what would it be and why? 

102. Tell me two truths and a lie, and let me guess which is which? 

103. What’s the weirdest/most interesting fact you know? 

104. Do you have any quirks that make you different to everyone else?

105. What could you not live without? 

106. Tell me the story about how you and your best friend met. Why do you think you both get along so well?

107. If you could ask God one question, what would you ask them and why? 

108. What event changed the direction of your life? 

109. What’s your spirit animal? 

110. Do you have any phobias? 

111. What brings a chill down your spine? 

112. Who do you secretly admire in your life? 

113. Would you rather be with someone who was clever or who was attractive?

114. What situations make you feel powerful? 

115. If you could tell your university self-one thing, what would it be? 

116. Do you like to take the lead on things or sit back and let someone else take charge? 

117. Have you ever secretly wanted to date a close friend of yours before? 

118. What does success mean to you? 

Looking For More Questions?

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A photo of Tom who is the Co-Founder of Questions About Everything

Tom Stevenson

Co-Founder of Questions About Everything

Tom is a travel writer and Co-Founder of Questions About Everything. He grew up in the UK and enjoys spending his time traveling to new places, supporting Liverpool FC, and blogging about his adventures. He spent two years teaching English in Barcelona and frequently utilized question games and conversation starters as part of his lesson plans. As an EFL teacher, he took full responsibility for planning and delivering lessons, frequently employing creative and diverse questions to engage the children in conversation. Learn more about Tom on our About page.